


Dean Winchester Headcanons

by justanotherbusyfangirl



Category: Supernatural
Genre: Aftercare, Blow Jobs, Cuddling & Snuggling, Dancing, Eating, Flirting, Hugging, Hunt, Kissing, Love, Nightmares, Pets, Sexuality, Singing, Stamina, Swimming, Threesomes, Underwear, Virginity, climax, sleeping
Language: English
Status: In-Progress
Published: 2018-12-05
Updated: 2018-12-05
Packaged: 2019-09-12 04:41:55
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 22
Words: 4,473
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16866334
Author URL: https://archiveofourown.org/users/justanotherbusyfangirl/pseuds/justanotherbusyfangirl
Summary: A collection of headcanons about Dean.  Some chapters are SFW, others NSFW.  Pay attention to the title of the chapter.





	1. Aftercare

While Dean doesn’t always stay the night after a hook up, he does make sure that his partner has been taken care of.  He knows as well as the next person that sticky things dry uncomfortably, and he doesn’t want anything the morning-after to be peeling off.

If there have been some kinky things going on, Dean also loves to soothe sore muscles with light massages.  Cleaning up and massaging the inner thighs, shoulders, or wrists and ankles after some rough or tied-up trysts is calming for both the giver and receiver, and it always continues the connection for long after the sex is over.


	2. Blowjob (receiving)

Dean’s first blowjob that he received was when he was 14, a freshman at some random school that he doesn’t even remember.  He had caught the eye of a junior named Annie, and she invited him to meet her behind the bleachers during one of the football games.  It took everything in him to convince John to go to that football game, as Sam was going to be home alone, but John eventually relented.

Annie was there when he arrived, wearing a low cut red tank top and dark blue skinny jeans, looking like the hottest thing Dean had seen – outside of magazines of course.  She had on this flavored lip balm that made her lips taste like strawberries, which was the first thing Dean noticed when she pulled him toward her by the collar of his jacket.

Dean, being Dean, tried to act cool and collected when Annie’s hands swiftly and surely unbuttoned and unzipped his pants, acting as though he’d had a girl touch him a hundred times.  He thought that’s what Annie would want him to act like.  

Thinking back, she could probably tell that it was his first blowjob by the sharp intake of breath when she first grasped his leaking cock in her hand, or maybe the way he whimpered when her lips wrapped around his purpling tip for the first time.  

She probably guessed, based on the fact that he had no idea where the proper protocol was for the placement of his hands – they hovered above her head, then moved to grab at the wall behind him, unsure if he was supposed to hold on to her for dear life or just stand there and take it.  

If none of the hesitant actions gave Dean away, she probably figured it was his first seeing as it only took a couple minutes of her bobbing, licking, and sucking for him to come down her throat.  The wet heat of her mouth was the most intense, exhilarating thing he’d ever felt around his virgin cock, and he was flushed with embarrassment mixed with arousal when Annie finally stood, wiping her mouth on the back of her hand before she kissed him again.

She walked away with a smirk on her face, leaving Dean to replay the moment over and over behind his eyelids, quickly becoming hard once more.


	3. Climax

Just like other aspects of sex, Dean has two ways of climaxing.

When he is hooking up with someone, a stranger, whom he doesn’t want to truly let in, Dean’s climaxes are what you could call manly.  He always makes his partner climax first, but when he finally gets to chasing after his own orgasm, he merely lets out a low grunt, scrunching his eyes up so that he can concentrate on the rush.  Sure, Dean likes coming like that just fine, but it’s not his first choice.

Dean’s first choice is to climax with someone he trusts, someone he loves. When he climaxes with that person, he really lets go.  There are whimpers, there are moans of their name.  He pants and sometimes tucks his face into the crook of their neck, feeling their pulse against his skin.  He usually tries to keep eye contact so that they can see how much he adores them, just by the release of passion that his climax brings.  Dean’s hips will slow, and he will draw it out as long as possible, so that they can truly be  _together_  for longer than just a moment.

 _That’s_  how Dean likes to climax.


	4. Cuddling

Don’t let Dean hear you say it out loud, but he enjoys cuddling.  It probably all started when he and Sam were kids and Dean would comfort Sam after a nightmare, but Dean definitely cuddles.

Now that he’s an adult and cuddling is usually expected before or after other more  _intimate_  acts, Dean is allowed to relish in the feeling more.  Post-sex naked, sweaty cuddling is his favorite kind.  Usually, if he’s with a girl, he doesn’t even have to instigate the cuddling – she will naturally curl up against his body as their heartbeats begin to slow.  If it’s a guy he’s been with, Dean still cuddles, but it will be less natural sometimes. There will still be a head resting on a shoulder or chest, arms wrapped around each other, but never for very long.

Non-sexual cuddling is good, too.  Dean really likes movie nights when they have friends in the bunker, and Dean ends up cuddled on the couch under a blanket.  Sometimes it’s with Charlie, her leaning into the crook of Dean’s arm, his head resting on top of hers.  Sometimes it’s with Jody, who treats Dean like a child by pulling him into her arms, threading her fingers through his hair and slowly putting him to sleep.  Sometimes it’s with Cas, who didn’t quite understand the point of cuddling at first, but has come to enjoy resting against Dean’s body. And sometimes still it’s his baby brother, the two of them sitting and enjoying the fact that they’re both still together, still alive, able to sit hip-to-hip with an arm around each other.


	5. Dancing

While Sam was away at Stanford and Dean was on his own for a bit, he learned that the quickest way to a woman’s heart (or in her pants) is through dancing.

Dean met a beautiful Hispanic girl at a bar in Texas and she knocked his socks off. They hit it off instantly, and had a wonderful night drinking, talking, and making love.  When Dean didn’t have to leave town immediately, he actually called her back the next day.  She was happy to host him again, but insisted that he come dancing with her.

She took Dean to a salsa lounge that she was apparently a regular at, and his eyes were opened to a world of dancing.  He watched for a while as couples twirled, glided, and moved together, before his partner took him out for a spin.  Dean could move – she knew that from their long night previously – but he had never moved in a vertical dance.

Dean learned a lot that night, and made it a habit to return to that salsa lounge any chance he got.  He used his dancing skills on a couple high-end hunts, which led him to learn other dances as well – tango, waltz, merengue, two-step.

Nowadays, Dean dances when he’s happy – to celebrate – or when he’s sad. Dancing lets him escape into a world where all that matters is him, his partner, and the music.  

Sam was a bit surprised the first time Dean grabbed him to spin him around the bunker after a big hunt, but once he realized that Dean wasn’t messing around and truly wanted to dance – and truly  _could_  dance – they spent the afternoon laughing and goofily dancing around the room.


	6. Eating

Food is important to Dean.  For so long when he was growing up, Dean didn’t know when he would get to eat. John didn’t always leave them enough money to buy food, so he often gave up his own meals to make sure that Sam ate properly.

Now that they’re adults and have a legitimate credit card scam going, Dean still never takes a meal for granted.  When they’re on a hunt, sometimes the boys aren’t able to stop for a bite to eat, all they can get is gas station grub.  Going to a diner and ordering whatever Dean wants (usually that medium-rare burger) is awesome when he has the chance.  He will cherish that burger for all it’s worth, enjoying the tastes in his mouth.

But more important than actually eating food, Dean enjoys the experience of eating - having his loved ones sitting around a table, enjoying company.  He will never give up the chance to sit and eat with his people: Sam, Jody, Cas, Claire - everyone.


	7. Flirting

For all it’s worth, Dean is a huge flirt.  He usually doesn’t mean it, however, as most of his flirting is to get them information or access to somewhere during a hunt.  Other times Dean flirts, it’s because he wants a quick lay to get out his pent-up energy and adrenaline after a hunt.

That being said, Dean has definitely earned the title of “Master Flirt.”  He can charm just about anybody, saying things that he knows people want to hear.  He knows all the right combinations of vocal inflection, lip movement, and intentional looks to make anyone’s insides turn to goo.

Sam may make fun of him for it, but Dean’s proud of his flirting abilities. He enjoys having the all the power, and he loves wrapping strangers and friends alike around his little finger.


	8. Hugging

To Dean, a hug is something important.  Growing up, he didn’t get many hugs.  He vaguely remembers his mom hugging him as a child, but once she was gone he didn’t get hugs from John.  He gave hugs to Sam when he had nightmares or was sad that dad wasn’t around, but he never received them.

When he was old enough, he found himself wanting hugs.  Wanting the feeling of comfort, of security, of love. Wanting the feeling of arms surrounding him, keeping him safe – but he knew that that feeling was a sign of weakness, and he more often than not pushed the thought from his mind.

As physical touch in the form of sex progressed in Dean’s life, he realized that he never got hugs from his hook-ups – that’s not the point of a hook-up, of course. There was holding, and arms around each other, of course, during sex, but the purpose of a hug should just be to  _hug_ , right?

Once Sam got back into the life, and he and Dean went through all of their trials and tribulations, Dean started receiving hugs from his brother.  He could never quite put into words how much those hugs meant to him, but finally being on the  _receiving_  end of a hug meant a lot.  After that, he received hugs from the other important people in his life as well – Jo, Bobby, John a few times, and Castiel.  

Those hugs mean something.  Those hugs were what hugs were supposed to be.


	9. Hunt

Dean’s first official hunt was an accident.  John had left Dean, only nine years old, and Sam in a cabin just outside of a town where he had followed some werewolves.  

John had taught Dean how to shoot by the time he was seven, so whenever he left the boys alone, he made sure Dean had a way to protect himself and his brother. Being on a werewolf case, John had left Dean a rifle and pistol, both loaded up with silver bullets.

Dean had just gotten his brother put to bed, around eight, and was sitting in the small living room of the cabin.  He was playing a card game of his own invention when he heard banging on the door.

Dean’s head shot up, knowing that it couldn’t be his father, as John had specific knocks that he used for any and all types of emergencies.  Dean grabbed the pistol, still way too big for his hand, but he could handle it fine, and backed up to stand in front of the door to Sam’s room.

The banging continued, rattling the door in its hinges.  Finally it shot open, and Dean came face-to-face with his first werewolf.

Instincts kicked in and Dean shot six rounds into the werewolf’s chest, the man teetering slightly before slumping to the ground.  Quickly, Dean reached for the rifle and extra magazine, setting them close so that he could get them if he needed.

He stood frozen, guarding Sammy’s doorway until John came back.  In fact, Dean almost shot John when he ran up to the open doorway, until his father’s face could be seen.

The werewolf, who had followed John’s scent to the cabin, was the first creature Dean killed, and he considers it his first hunt, at just nine years old.


	10. Kissing

Even though he’ll never admit it, one of Dean’s favorite parts of being with someone is kissing them.  You can tell a lot about a person from how they kiss.  Dean’s kisses are usually sweet, letting affection or need show through smooth motions of his lips and tongue.  It’s one thing he can do in his life that is gentle, and he enjoys that. Sometimes, though rarely, Dean will be rough with his kisses, letting teeth clash together and seemingly devouring their tongue.

Dean enjoys learning the taste of their tongue, holding their face close as they breathe each other’s air.  Dean loves the way his nose will press against his partner’s, the closeness showing how much they want each other.  Dean takes the time to explore everything about his partner’s lips, mouth, and tongue. He likes to nibble gently, earning either a moan or a giggle, depending on the situation.  

Dean likes to kiss along his partner’s jawline, making them tilt their heads to give him more room to work.  He feels successful when they sigh or moan from the attention, and makes sure to find all their sensitive places.


	11. Love

There are many ways that Dean says “I love you” without saying those three words.

Sometimes it’s physical touch – an extra long hug, a pat on the knee, a punch on the shoulder.

Sometimes it’s acts of kindness – carrying Sam’s bag into the motel for him, making breakfast or dinner, going grocery shopping for the bunker, saving the last piece of pie.

Sometimes it’s said through other words: “I believe in you,” “You’re important to me,” or “I’m here for you.”

Rarely, so few times that others know to cherish it when he does, Dean will actually say those words.  When Dean says “I love you,” it’s one of the most intense and sincere things to ever leave his lips.


	12. Nightmares

Dean’s never talked to anyone about his nightmares, not Sam, not Cas, not even Lisa or any of the partners he’s woken up in the middle of the night.

Of course, he’s got nightmares of his time in hell – that experience will forever haunt him.  

He’s got nightmares of his year in purgatory, of what might have happened if he hadn’t met and teamed up with Benny, of what might have happened to Cas, of how he could still be trapped there if not for that one portal…

He’s got the generic nightmares of people who he loves dying – Sam, Mary, Castiel. He’s got the real memories of deaths that plague him – Charlie, John, Bobby.

Dean copes with those nightmares.  They’re a part of him.  He has learned to use them to make him stronger, to encourage him to push on and fight.

But to this day, the worst nightmares of all are the ones when he relives the night of the fire.  Nightmares where instead of being able to save baby Sam, he is forced to watch as the crib is engulfed in flames.  Nightmares where four-year-old Dean is powerless to save his brother.  Those nightmares, those altered memories, are by far the worst that he has.


	13. Pets

Dean hasn’t ever really wanted a pet.  Sure, he doesn’t mind animals every once and a while, and Colonel, the dog who he bonded with on that one case, was a pretty awesome dog, but he’s never felt the need to get a pet.

They’re a lot of work, pets.  You have to feed them, bathe them, exercise them, take care of them.  Dean’s already got a job – saving people, hunting things. Adding “taking care of Roxie” doesn’t quite fit with that list.  It would be one more thing to do, and one more being for him to take care of, a list which is already extensive.

In the back of his mind, Dean also doesn’t want to think what would happen to his pet if one day he doesn’t return from a hunt.  Better to just not have an animal grow to love and depend on him, right?


	14. Singing

While Dean might not be the greatest singer in the world, he enjoys singing a lot. He will belt out songs in the car, pretending that he does it to annoy Sam during a long drive, but really it’s because he loves to sing.  He knows he doesn’t have the best voice, but he doesn’t care.  Singing is one way that Dean can express himself – through the story of someone else.  

Sometimes he’ll find a song that truly relates to what he’s feeling. Something sad or angry – that’s when he stays quiet.  Instead of singing along, he appreciates the singing of the performer.


	15. Sexuality

Dean doesn’t much like to define things.  When it comes to relationships or one-nighters, he doesn’t like to put himself in a box.  He just knows what he loves.

Dean loves women.  He loves the curves of their bodies and how soft their skin is.  He loves threading his fingers through their hair as they kiss, sometimes pulling on it slightly, just for fun.  He loves the way he fits between their legs when they fuck.  He loves the sounds he can pull from between a woman’s lips, high-pitched and wanting.  Dean loves women.

Dean loves men.  He didn’t realize it until he was a little older, but he loves the way a man will take charge.  He loves not having to think or control the situation.  He loves being manhandled, pulled against a firm body and kissed until he can’t breathe.  He loves the feeling of his 5 o’clock shadow rubbing against another’s.  He loves the angular nature of his hips fitting against another’s – cocks grinding hard.  He loves being pulled and stretched and opened up under cool and confident hands.  Dean loves men.


	16. Sleeping

Dean has learned to be a light sleeper.  After growing up on the move, dad sometimes waking them up to go somewhere new in the middle of the night, Dean having to get Sam packed and in the car, Dean rarely goes  _deep_  into sleep.

He always keeps a weapon under his pillow, whether it’s a knife or his gun, he just needs to know that he can fight at a moment’s notice.  

Of course, the motel beds they usually stay on aren’t comfortable enough to sleep soundly on anyways, with the lumpy mattresses and squeaky bedframes.  Dean never could sleep well in motels.

Then they found the bunker.  And his bed had memory foam –  _it remembers him_.  And he doesn’t have to worry about things breaking into his room at night.  (Although he keeps three guns in the room, ready to go – one in the bedside table, one under the mattress, and one in his top dresser drawer, but that’s besides the point.)

When he’s sleeping in the bunker, he can relax.  It took him a while to get used to it, but once it really sunk in that he could get quality rest at the bunker, Dean started sleeping like a baby.

As for sleeping with a partner….well, Dean  _really_ likes it when a warm body is snuggled up against his side, their breath fanning across his chest.  He is usually too caught up with feeling their body against his, watching  _them_  sleep to get much rest himself, but it is  _definitely_  nice to have someone to sleep with.


	17. Stamina

When Dean was in his teens and twenties, he prided himself on his ability to go round after round of sex.  He thought he was the god of stamina.  He was constantly wearing out his partners, wanting to fuck over and over again whenever they would spend the night together.  Not only would his body recover quickly, but he would constantly push his partner to orgasm over and over again, wearing them out before he even considered quitting.

Now that Dean is a little older, his stamina has changed a bit.  Yes, he still wants to go all night long, but he makes each moment last.  He can’t quite get it up as quickly as he used to, so he has altered his goals.  Instead of having a lot of orgasms, the intensity of sex has increased, because Dean appreciates it more.  He knows that he won’t live forever, so he wants to make the most of the time he has left.  If that means that having sex is slow and soulful, that’s what Dean wants.


	18. Swimming

Dean learned how to swim out of necessity, not out of exercise or entertainment.  He was on a hunt with John when he was 11 or 12, Sam having stayed back with Bobby. He couldn’t remember the details, as the whole experience was somewhat traumatic, but he does remember that there was a lake, and Dean fell into it.  

It took John almost 20 minutes to finish the kill before he could start to look for Dean.  By that point in time, Dean thought that he was close to drowning four or five times, his arms and legs exhausted from kicking and holding his head above water.

Through trial and error, Dean figured out how to do a modified doggy-paddle/breast-stroke, and John found him wet and tired, halfway to the shoreline.

Dean didn’t want to swim much for a few years after that, but eventually got over his fear of swimming and made sure that his little brother knew how to swim, so Sam would never be as scared as Dean was in the water, ever.


	19. Threesomes

Dean prides himself on being up for anything.  The first threesome he was a part of (when he was only 18), he was basically tricked into it.  He found a girl at a bar, went to her motel room to find her friend as a surprise, tied up on the bed.  That threesome was fun for him, as the girls were all about him that night.  Yes, he gave them each a couple orgasms, but they were all over him, and he had no complaints whatsoever.

A couple years later, he found himself in another surprise threesome situation, this time a little different.  He picked up a girl at a bar, and as they were walking out they made a pit-stop at the door to make out a bit.  A tap on Dean’s shoulder had him turning to see a very attractive guy, saying if Dean took his girl home, he would be taking the both of them home. Having had quite a bit to drink and an optimistic attitude, Dean agreed.  Dean and the guy didn’t have much interaction, the action was pretty exclusively with the girl between them.  Dean couldn’t help but looking, however, and definitely enjoyed himself more than he did with usual two-somes.

After that, Dean found himself in more and more multi-partner experiences, with both genders.  As he got more comfortable with the available options and positions, he became more outgoing as well.  While he still has never had a male-exclusive threesome (it may or may not be on his bucket list), he definitely enjoys all partners in all ways possible, whenever he’s allowed.


	20. Underwear

When you travel as much as a Winchester does, and clothes are bought in necessity, not luxury, you don’t take a lot of time to choose fancy-pants underwear.

Dean wears boxers.  Cheap and simple, the kind that come in packs of eight or ten.  He knows that anyone who sees them will be too distracted by his talent and physique that they won’t ever been judgmental of his cheap underwear.

As long as it’s not itchy, Dean’s happy.


	21. Virginity

With the lifestyle that John led them on as kids, Dean’s virginity wasn’t a big deal to him.  He started reading porn magazines when he was only 10, and watched his first Casa Erotica when he was 13.  Since John was away so much and they moved around a ton, Dean often had unsupervised guests over, starting at the age of 15.

He lost his virginity the summer after he turned 15, to a girl who was 17.  He kicked Sam out of the room for a couple hours, and let her take the reigns.  She was nice to him, but also berated him a bit for not knowing everything.  He went back to visit her a couple times by himself once he could drive, letting her teach him about a woman’s body and how to make her feel good.

When it came to Dean taking someone’s virginity, he didn’t care much about it until he was much older.  He knew he was the first for six girls he met in his late teens, but at that point in his life all he wanted was some fun before dad made them leave town.

Once Sam left for Stanford, things changed a bit.  Dean was growing up, and realized that there are things in life that should be special.  He made sure that any other girls whose virginity he took felt special and loved, if only for that one night.  He made their first time good and comforting, and wished that his first had been that way as well.


	22. Zzz's

Dean’s one of those people who goes one of two ways.

Option one: the sex was obviously a one-night stand, and he’s out of there as soon as things have been cleaned up.  It might have been quick and dirty, or even just need-pleasing, but once the do is done, he’s up, dressed, and out.   He might be going back to sleep his four hours in the motel room he’s sharing with Sam, or he might be getting in Baby and driving three states over for their next hunt, but the point is – there’s no cuddling and sleeping.  Dean’s outta there.

Option two: the sex meant something.  It wasn’t  _just_  sex.  He’s comfortable with the person, because they’re not just a stranger he met in a bar, they’re someone he knows – someone he loves in one way or another.  If the sex meant something, he puts his all into the act, physically  _and_ emotionally.  Dean isn’t someone who regularly lets his emotions out, and it’s exhausting to him. All he wants to do after raw, emotional, soul-draining sex is wrap his partner up in his arms and fall asleep, swiftly and easily.


End file.
